(2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

Base Information

Chemical Name:(2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine
CAS No.:863392-58-9
Molecular Formula:C₂₀H₂₄N₂O₇S₂
Molecular Weight:468.552
Hs Code.:

Synonyms:(2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

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Chemical Property of (2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

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Technology Process of (2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

There total 4 articles about (2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

: 118329-82-1
(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

: 3019-71-4
Trichloroacetyl isocyanate

: 863392-58-9
(2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

Guidance literature:: (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine; Trichloroacetyl isocyanate; In dichloromethane; at 0 ℃; for 2h;

With potassium carbonate; In methanol; at 0 ℃; for 4h;
DOI:10.1016/j.tetlet.2005.06.025

Reference yield:

: 118329-81-0
(2S,4R)-2-ethoxycarbonyl-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

: 863392-58-9
(2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 91 percent / NaBH₄; LiCl / tetrahydrofuran; ethanol / 3.5 h / 0 °C

2.1: CH₂Cl₂ / 2 h / 0 °C

2.2: 91 percent / K₂CO₃ / methanol / 4 h / 0 °C

With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/j.tetlet.2005.06.025

Reference yield:

: 51-35-4,30724-02-8
4R-4-hydroxyproline

: 863392-58-9
(2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / SOCl₂ / 5 h / Heating

2.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h / 20 °C

3.1: 91 percent / NaBH₄; LiCl / tetrahydrofuran; ethanol / 3.5 h / 0 °C

4.1: CH₂Cl₂ / 2 h / 0 °C

4.2: 91 percent / K₂CO₃ / methanol / 4 h / 0 °C

With dmap; sodium tetrahydroborate; thionyl chloride; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/j.tetlet.2005.06.025